How do you pick just a handful of songs from the 40-year career of rock’s most esteemed, chameleon-like, oft-copied (never duplicated), guitar-thrashing icon? You do what Neil Young himself has done through the decades: Throw caution to the wind and go with your heart.

Maybe he’s the best guy to pick his own songs. On his current tour of sold-out theater shows—which stops in Buffalo at Shea’s Performing Arts Center tomorrow night—Young has gracefully pulled off astounding sets, mixing solo acoustic portions interspersed with full-band parts. It has found him pulling gems from the very beginning of his career to his most recent album, Chrome Dreams II (Reprise), and picking established classics, fan favorites and some real surprises.

My Neil Young playlist? Kinda like that. Given Neil’s affinity for all things analog, maybe I ought to call it a mix tape. Either way, here’s a chronological trip through some of Neil Young’s finest moments that goes down the road, into the ditch and back again a few times.

“Mr. Soul” by Buffalo Springfield from the album Buffalo Springfield Again

Like the ultimate collision of the Beatles and the Stones—the Springfield’s noted, primary influences—packed with every kind of guitar sound you could want: chiming, distorted and even backward. Often Young willingly took a back seat to Richie Furay and Stephen Stills, but this is one of the few moments where Young took a lead vocal and ultimately provided the Springfield with their best, true and blue rock-and-roll anthem.

“Expecting to Fly” by Buffalo Springfield from the album Buffalo Springfield Again

Sort of a yang to the yin of “Mr. Soul,” this is an echoey, grandiose mini-symphony, complete with strings, which makes for a gorgeous, dreamy four minutes and starts to hint at the depth and breadth of Young’s songcraft.

“Cowgirl in the Sand” from Everybody Knows This Is Nowhere

A sprawling, spiraling, 10-plus-minute, psych-rock masterpiece written by Young in a literally fevered panic and enacted with the kerosene jamming of the Rockets, who would go on to become his loud and perfectly imperfect regular band, Crazy Horse. You could trade it out for the equally inspired epic “Down by the River,” also from the album Everybody Knows This Is Nowhere.

“After the Goldrush” from After the Goldrush

Young’s serene and surreal tale of silver spaceships and utopian grace eloquently ushered in a new decade and subtly eyed ecological concerns, without ever breaking from the beauty of the song that features the lines, “Look at Mother Nature on the run/In the 1970s.” Who would have guessed that this unpretentious and elegant song was inspired by an unproduced screenplay penned by character actor Dean Stockwell?

“Helpless” from Massey Hall—January 12, 1971

An elegant version stripped of all but voice and acoustic guitar that surpasses the overproduced original from Crosby Stills, Nash and Young’s Deja Vu.

“Out on the Weekend” from Harvest

This countrified, Bob Dylan-inspired number—complete with wailing harmonica and even name-checking the “big brass bed” from “Lay Lady Lay”—finds a protagonist rife with unsureness and deep longing that makes it the perfect, downtrodden flipside for those for whom the Friday night party song isn’t the right fit.

“Journey Through the Past” from Time Fades Away

Recorded in 1971 and issued on the now criminally out-of-print live album Time Fades Away, it’s just Neil and a piano in what sounds like a triptych of his life. He wonders if he will still be in the ears and on the mind of the one he left behind. The wrenchingly bittersweet song is marked by the kind of wonderfully warts-and-all, soul-laid-bare performance that would never make it to a record these days.

“Walk On” from On the Beach

This jangly, rambling and upbeat opener is a little out of step with the rest of On the Beach, an album haunted by the specters of the Nixon administration, Charles Manson, energy and environmental concerns and the deflated hippie dream. But the song’s lyrics provide some of the ultimate statements of the Young ethos. Like he says, “They do their thing, I’ll do mine.

“Ambulance Blues” from On the Beach

Another track from what is arguably Young’s best album, this bleak, bleary-eyed, nine-minute narrative shifts between past and present. While the arrangement is spare, the song is lyrically bursting at the seams, rife with pastiches and imagery that puts the Toronto clubland of Young’s “folkie daze” alongside Navajo trails, kidnapper’s ransoms and lying politicians. It seems to decry a wanton turn in society and a loss of innocence. It has become a surprising and welcome staple of the set list on this tour.

“Borrowed Tune” from Tonight’s the Night

With just a harmonic, piano, his creaky voice and a “borrowed tune” from the Rolling Stones, Young delivers an intimate and devastatingly perfect comedown ballad of wasted perfection from an album about how being so wasted only leads to destruction.

“Cortez the Killer” from Zuma

Neil’s ultimate jam song. Many bands have tried it on for size but none have matched the meat that he and Crazy Horse make here. He and Frank “Pancho” Sampedro smoke the strings and melt faces as they tear this one apart.

“Bite the Bullet” from American Stars ’N Bars

On this unbridled bar rocker, Neil sings—in no uncertain terms—about how to really please a woman: Bite the bullet.

“Hey Hey, My My (Out of the Blue)” from Rust Never Sleeps

Another enduring Young anthem, this one both seemingly both celebrating and deriding the rock-and-roll life. It’s crushing, electrified twin “Hey Hey, My My (Into the Black)” closes the album.

“Thrasher” from Rust Never Sleeps

Like On the Beach, you can’t pick just one from this album, and “Thrasher” is another moment of acoustic perfection in the form of a vaguely futuristic/end-of-days story that masks a surface not so far below a message about how people change and have to be left behind. Neil has admitted it to be about his friends and bandmates, Crosby, Stills and Nash.

“Wonderin’” from Everybody’s Rockin’

A terrific song that Young had kept sitting around for years until it was refigured as a rockabilly/doowop number in 1983.

“F*!#in’ Up” from Ragged Glory

Young returned to former glory on Ragged Glory with Crazy Horse in tow. This bashing explosion of garage rock furor lyrically bears more than a hint of doubt and nihilism, unwittingly setting the pace for a decade that yielded Pearl Jam and Nirvana.

“From Hank to Hendrix” from Harvest Moon

A mellow paean to country and rock and roll that bookends the Hillbilly Shakespeare and the left-handed Stratocastor banshee.

“Stringman,” live version from Unplugged

Reportedly part of the unissued 1977 album Chrome Dreams, it’s song partly about mourning and about having a change of heart and doing what you believe is right. The gentle acoustic number remained in the vaults among the vast Neil Young archive until he unearthed it for 1993’s Unplugged, culled from his appearance on the MTV program of the same name.

“Carmichael” from Greendale

In another hypnotic, 10-minute burner where he’s aided by Crazy Horse, Young delves into the story of a cop killed in the line of duty and the details of his life that come to forefront in death. It’s one of the finest moments from Young’s intriguing 2003 concept album.

“Spirit Road” from Chrome Dreams II

Hardly one to take a rest or rest on laurels, Young’s latest record is a sequel to a record he never released. Here’s a feedback-laden blast of twisted, snarling rock that wouldn’t sound out of place on Rust Never Sleeps. It belies a guy in his 60s, but then again this is Neil we’re talking about. Naturally, this old man still fires on all cylinders. Long may he continue to run.